When the person who committed the crime not only tried to take a shot at a cop, but is subsequently deemed a habitual criminal, thereby multiplying the sentence in a big way. Which is precisely what happened to Randy Keesee.

During his career on the far side of the law, Keesee, 45, racked up five felony convictions. This track record transformed any future serious offense into the equivalent of the straw that broke the camel's back.

Cut to an April day in 2010 when, according to the Jefferson County District Attorney's Office, Keesee walked into the Famous Bonanza Casino in Central City armed with a semi-automatic. He then approached a pair of cashiers demanding money, and they complied, handing him $28,000.

Keesee split with a bag filled with cash, escaping the joint without further incident. But the ease with which he got away apparently emboldened him, because shortly thereafter, he was back in a casino, albeit a different one -- the Golden Gate in nearby Black Hawk. He was reportedly contacted by a Black Hawk police office, who had spotted the alleged getaway car, a black Audi, in the parking garage and suspected that Keesee was the driver.

At that point, Keesee allegedly drew his weapon and tried to shoot the cop, but his gun malfunctioned. That wasn't the case with the officer's gat, however. In a particularly dry phrase, the DA's office notes that "Keesee was injured when the officer fired back" -- and his booking photo definitely makes him look worse for the wear.

The following November, a jury found Keesee guilty of attempted first-degree murder, four counts of aggravated robbery, first degree assault of a peace officer, theft of over $20,000 and reckless endangerment. Because the violent crime counts served as sentence enhancers in light of his habitual-criminal status, he was sentenced at four times the maximum he would have otherwise received for his actions: 224 years.

Clearly, his gamble didn't pay off. Look below to see a larger version of Keesee's booking photo.